If you’ve ever walked around SoHo, maybe perusing the stores along Prince Street or Houston, then you’ve more than likely stepped foot into the bustling neighborhood known as Hudson Square. Originally the city’s Printing District, Hudson Square encompasses the area from Canal Street to West Houston and 6th Avenue all the way to West Street. Despite its close proximity to SoHo and relatively small size, Hudson Square is a unique area distinguished by its historical significance, from a 200-year old bar to George Washington’s former headquarters.

In addition, the neighborhood maintains a thriving cultural space marked by inviting outdoor gathering spaces, art galleries and modern architecture, as well as fantastic restaurants, trendy coffee shops, and eclectic bars. Conveniently, this fun, thriving area is extremely accessible by subway, so make sure to check our these 20 must-visit places if you ever find yourself in Hudson Square:

Historic Sites:

Ear Inn

Photo via Hudson Square Connection

This historic establishment was originally built in the late 18th century as a home for James Brown, an African-American veteran of the Revolutionary War, aide to George Washington, and proprietor of a tobacco store housed on the ground floor. After changing hands during the early 1800s, the two story townhouse was eventually turned into a tavern and is now recognized as one of the oldest existing bars in New York City.

The Ear Inn has gone through many changes over the years, from tobacco store and home to tavern, brewery, restaurant, then during Prohibition to a speakeasy, brothel, boarding house, and smuggler’s headquarters, and finally to the bar it is today. Purchased in the 1970s by a group of artists, the bar took on the name of The Ear Inn due to restrictions on altering historic buildings. The owners simply painted out part of the “B” in the bar sign, turning it into the word “Ear,” which also happened to be the name of a music magazine published upstairs. Location: 326 Spring St., New York, NY 10013.

The SoHo Playhouse

The playhouse occupies the land on which once stood Richmond Hill, a colonial mansion built in 1767 and owned by British Major Abraham Mortier. It served as the headquarters for many historic figures, including Lord Jeffrey Amherst, George Washington, and Sir John Temple, as well as the official residence of John Adams and later of Aaron Burr.

The estate was later sold to businessman and real estate giant John Jacob Astor, who then opened the house and its gardens as a public resort in 1822. From then until its demolition in 1849, the mansion served as a theater, Italian opera house, and a saloon. In the later 1800s, 15 Vandam Street, the location of the current playhouse, was designated as The Huron Club and meetinghouse of Tammany Hall. Finally, into the 20th century, the location housed a speakeasy and theater, the Playwrights Unit Workshop, the independent cinema Film Forum, and is now home to the Off-Off Broadway theater SoHo Playhouse. Location: 15 Vandam St., New York, NY 10013.

Charlton-King-Vandam Historic District

The Charlton-King-Vandam area encompasses parts of the three streets between Avenue of the Americas and Varick Street as well as the streets bounded by King, MacDougal, and Houston Streets and Sixth Ave. Recognized as a Historic District and New York City Landmark, the area was once part of the Richmond Hill estate.

The district is recognized largely for its exceptional architecture, which features row houses built in the Federal and Greek Revival styles. Charlton and Vandam Streets display the majority of these houses, while King Street showcases Roman Revival style houses as well as the former Public School 8 built in 1886. Location: roughly the streets bounded by Vandam, Varick, West Houston, MacDougal Streets and Sixth Ave.